HCID 68992721, compound → HCID 23647767, compound

HRID 1725936Notes

Reaction equation

HRID 1725936 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:17]([C:18]([O:20]CC3C=CC=CC=3)=[O:19])=[C:16]([CH3:28])[C:15]([CH:29]([OH:31])[CH3:30])=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>CO.O.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C:12]2[C:17]([C:18]([OH:20])=[O:19])=[C:16]([CH3:28])[C:15]([CH:29]([OH:31])[CH3:30])=[CH:14][CH:13]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 68992721HCID 68992721, compound

Product 1

HCID 23647767HCID 23647767, compoundYield 65.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of Example 272A (79 mg, 0.22 mmol) in methanol (8 mL) and water (1.0 mL) was treated with 10% Pd/C (160 mg) and stirred under hydrogen for 16 hours. Filtration and solvent evaporation gave the desired compound (51 mg). 1H NMR (DMSO-d6) δ 1.23 (s, 3H), 2.21 (s, 3H), 4.87 (m, 1H), 5.06 (br s, 1H), 6.82 (d, 1H), 7.36-7.41 (m, 3H), 7.78-7.82 (m, 2H), 10.4 (s, 1H), 13.2 (br s, 1H); MS (ESI(−)) m/e 352 (M−H)−.

Workup

  1. filtrationFiltration and solvent evaporation

Sources & evidence

ORD record
ord-d94290326d5b4d07ba3dc9bb9962d6a3
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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